50892-62-1

Usage

Uses

Used in Pharmaceutical Industry:
8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one is used as an intermediate in the preparation of pharmaceutical actives for its potential role in the development of therapeutic agents.
Used in Fine Chemicals Industry:
8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one is used as an intermediate in the preparation of fine chemicals, highlighting its versatility and applicability in various chemical synthesis processes.
Used in Antipsychotic Drug Development:
8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one is used as a key intermediate in the synthesis of antipsychotic drugs, contributing to the development of novel treatments for mental health disorders. Its unique chemical structure allows for the creation of compounds with potential therapeutic benefits in managing the symptoms of various psychiatric conditions.

InChI:InChI=1/C13H9ClN2O/c14-8-5-6-11-12(7-8)16-13(17)9-3-1-2-4-10(9)15-11/h1-7,15H,(H,16,17)

Upstream product

• 67990-66-3 N-(2-Amino-4-chlorophenyl)anthranilic acid 
• 41513-04-6 2-chloro-5-bromonitrobenzene 
• 60091-87-4 2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure 
• 118-92-3 anthranilic acid 
• 89-61-2 2,5-dichloronitrobenzene 
• 28144-70-9 anthranilic acid amide 
• 881-51-6 N-(4-chloro-2-nitrophenyl)-acetamide 
• 89-63-4 4-Chloro-2-nitroaniline 
• 108-88-3 toluene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 106-47-8 4-chloro-aniline 
• 539-03-7 N-(4-chlorophenyl)acetamide 

Downstream Products

• 81469-85-4 8-Chloro-11-(octahydro-pyrido[1,2-a]pyrazin-2-yl)-5H-dibenzo[b,e][1,4]diazepine 
• 6104-71-8 N-desmethylclozapine 

Relevant academic research and scientific papers

Hydrazides of clozapine: A new class of D1 dopamine receptor subtype selective antagonists

Acylated and aroylated hydrazinoclozapines are highly potent dopamine D1 antagonists that show remarkable selectivity over other dopamine receptors. The most potent compound in this series is the 2,6-dimethoxybenzhydrazide 33 with a D1 Ki of 1.6 nM and 212-fold selectivity over D2 receptor.

Synthesis and pharmacological evaluation of 11-(1,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-dibenzo[b,e][1,4]diazepines with clozapine-like receptor occupancy at dopamine D1/D2 receptor

Clozapine-like compound without agranulocytosis risk is need to cure the treatment resistant schizophrenia (TRS). We discovered (S)-3 as Clozapine-like dopamine D2/D1 receptor selectivity and improved reactive metabolites formation profile by the modification of piperazine moiety in Clozapine. The optimization of (S)-3 gave compound 5 to be best compound (approximately 10-fold stronger affinity for D2/D1 receptor and similar D2/D1 selectivity ratio with Clozapine). Clozapine-like D2/D1 receptor occupancy profile was proved by in vivo evaluation. In addition, the reactive metabolites derived agranulocytosis risk of compound 5 was considered to be lower than Clozapine. The pharmacology detail of compound 5 is being investigated to develop it for TRS treatment.

BROAD SPECTRUM GPCR BINDING AGENTS

Provided herein are broad-spectrum G-Protein coupled receptor (GPCR) binding agents, detectable/isolatable compounds comprising such binding agents (e.g., broad-spectrum GPCR binding agents linked to a functional element and/or solid surface), and methods of use thereof for the detection/isolation of GPCRs.

Clozapine intermediate as well as synthesis method and application thereof (by machine translation)

The invention discloses a clozapine intermediate and a synthesis method and application thereof, and belongs to the technical field of drug synthesis. The synthesis method comprises 1) synthesis of 2 - [(2 - amino -4 - chlorophenyl) amino] benzoic acid, 2) 8 - chlorine -5, 10 - dihydro - 111111H-dibenzo [b, e] [1, 4]-diazepine -11 - ketone. The synthesis method of the clozapine intermediate is simple in preparation process, recyclable in solvent, easy to operate and control, good in color, good in quality, high in purity and high in yield, can be directly used for production and use, and has good practicability. (by machine translation)

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5 H -Dibenzo[ b, e ][1,4]diazepin-11(10 H)-ones

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N -aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N -aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Method for preparing clozapine intermediate

The invention discloses a method for preparing a clozapine intermediate. The method comprises the following steps: (a) dissolving NCNA (N-(4-Chlorine-2-Nitrobenzophenone) o-aminobenzoic acid) sylviteinto water so as to obtain an NCNA sylvite solution; (b) sequentially putting ferric trichloride and activated carbon into the NCNA sylvite solution, uniformly mixing so as to obtain a mixed solution,and adjusting the pH value of the mixed solution to 9-12 by using an alkali solution; (c) heating the mixed solution, dropping a hydrazine hydrate solution into the mixed solution till the mixed solution is completely decolored, heating and filtering for another time, and collecting filtrate; (d) tittering the filtrate till the pH value is 3-5 by using dilute sulfuric acid, and collecting a separated solid; (e) backflowing the solid with the dilute sulfuric acid, thereby obtaining 8-chlorine-5,10-dihydro-11H-dibenzo [b,e] [1,4]-diazepine-11-ketone. By adopting the method disclosed by the invention, introduction of an organic solvent is avoided, production at normal pressure can be achieved, the production security is high, the production cost is low, and in addition, the method is high inyield and small in impurity.

NOVEL and IMPROVED SYNTHESIS OF ANTIPSYCHOTIC DRUG

The present invention relates to novel as well as improved process for the preparation of Clozapine of Formula I which involves anti-narcotic and highly cost effective raw materials.

Palladium-catalysed regioselective: N -arylation of anthranilamides: A tandem route for dibenzodiazepinone synthesis

A palladium-catalyzed domino approach to the synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepinones from 2-aminobenzamides and 1,2-dihaloarenes has been developed. Our strategy integrating double N-arylations (inter- and intra-molecular) of 2-aminobenzamides with 1,2-dihaloarenes under palladium-catalyzed conditions is clearly distinct from the current literature available for the synthesis of dibenzodiazepinones. Unlike a previous report described for regioselective N-arylation of 2-aminobenzamide at the amine group, our mechanistic studies support the regioselective N-arylation of 2-aminobenzamide occurring first primarily at the amide group. The translational application of our protocol may be demonstrated in the synthesis of a marketed drug, clozapine.

Synthetic method of key intermediate for preparing clozapine

The invention discloses a synthetic method of a key intermediate for preparing clozapine, and belongs to the field of drug synthesis. The method comprises the step that 2-((2-amino-4-chlorphenyl)amino)benzoic acid is taken as a raw material to be cyclized under backflow of a sulfuric acid water solution, and 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]-dinitro-11-ketone. The formula is shown in thedescription. The synthetic method utilizes the sulfuric acid water solution to conduct cyclization, and overcomes the multiple defects in the prior art, the reaction is simple, convenient and rapid,the impurities introduced by the raw material can be effectively removed, the product with the higher purity is obtained, and the waste liquid is easy to treat. Meanwhile, increasing cost and environmental pollution caused by using of other solvents are avoided, and the synthetic method has the good industrialized prospect.

Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase

This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.